Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Alpha-Hydroxyisobutyric acid (HMDB00729)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:11 -0700
HMDB ID HMDB00729
Secondary Accession Numbers None
Metabolite Identification
Common Name Alpha-Hydroxyisobutyric acid
Description Alpha-Hydroxyisobutyric acid is a metabolite of methyl tert-butyl ether (MTBE). MTBE may be obtained through environmental exposure. MTBE is rapidly eliminated from the body, mainly through expired air as the unchanged compound. MTBE is to some extent metabolised to t-butyl alcohol (TBA) and formaldehyde and oxidised to 2-methyl-1,2-propanediol and a-hydroxy isobuturic acid. Alpha-Hydroxyisobutyric acid has been used as an arial bactericide.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (ch3)2cohcooh
  2. 2-Hydroxy-2-methylpropanoate
  3. 2-Hydroxy-2-methylpropanoic acid
  4. 2-Hydroxy-2-methylpropionate
  5. 2-Hydroxy-2-methylpropionic acid
  6. 2-Hydroxyisobutyrate
  7. 2-Hydroxyisobutyric acid
  8. 2-Methyllactate
  9. 2-Methyllactic acid
  10. a-HIB
  11. a-Hydroxy-a-methylpropanoate
  12. a-Hydroxy-a-methylpropanoic acid
  13. a-Hydroxyisobutanoate
  14. a-Hydroxyisobutanoic acid
  15. a-Hydroxyisobutyrate
  16. a-Hydroxyisobutyric acid
  17. Acetonate
  18. Acetonic acid
  19. alpha-HIB
  20. alpha-Hydroxy-alpha-methylpropanoate
  21. alpha-Hydroxy-alpha-methylpropanoic acid
  22. alpha-Hydroxyisobutanoate
  23. alpha-Hydroxyisobutanoic acid
  24. alpha-Hydroxyisobutyrate
  25. alpha-Hydroxyisobutyric acid
  26. HIBA
  27. Hydroxydimethylacetate
  28. Hydroxydimethylacetic acid
  29. Hydroxyisobutyrate
  30. L-2-Methyllactate
  31. L-2-Methyllactic acid
Chemical Formula C4H8O3
Average Molecular Weight 104.1045
Monoisotopic Molecular Weight 104.047344122
IUPAC Name 2-hydroxy-2-methylpropanoic acid
Traditional IUPAC Name α-hydroxy-isobutyric acid
CAS Registry Number 594-61-6
SMILES CC(C)(O)C(O)=O
InChI Identifier InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
InChI Key BWLBGMIXKSTLSX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Hydroxy Acids and Derivatives
Sub Class Alpha Hydroxy Acids and Derivatives
Other Descriptors
  • 2-hydroxy fatty acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Hydroxy fatty acids(Lipidmaps)
  • branched-chain fatty acid(ChEBI)
  • short-chain fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Tertiary Alcohol
Direct Parent Alpha Hydroxy Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Toxin/Pollutant
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 82.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.36 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 378 g/L ALOGPS
LogP -0.37 ALOGPS
LogP -0.039 ChemAxon
LogS 0.56 ALOGPS
pKa (strongest acidic) 3.95 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 23.55 ChemAxon
Polarizability 9.87 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
8.2 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
7.0 (0.0-9.0) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
2.9 (1.3-4.6) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Urine Detected and Quantified
Article_icon
3.80 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
Article_icon
0.1 (0.1-3.8) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
6.2 (3.8-14.1) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 6-10 years
Urine Detected and Quantified
Article_icon
5.5 (2.9-10.3) umol/mmol creatinine Adolescent (13-18 years old) Both Normal >10 years
Urine Detected and Quantified
Article_icon
7.9 (3.7-19.5) umol/mmol creatinine Children (1-13 year old) Both Normal Children aged 2-6 years
Urine Detected and Quantified
Article_icon
0.1 (0.1-8.2) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
3.8 (1.7-5.9) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
5.0 (0.0-8.0) umol/mmol creatinine Not Specified Both Lung cancer Not Available
Associated Disorders and Diseases
Disease References
Lung Cancer
    • HMP expermental
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022207
    KNApSAcK ID Not Available
    Chemspider ID 11181 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB00729 Link_out
    Metagene Link HMDB00729 Link_out
    METLIN ID 3750 Link_out
    PubChem Compound 11671 Link_out
    PDB ID Not Available
    ChEBI ID 50129 Link_out
    References
    Synthesis Reference Vogl, O. Synthesis of a-hydroxyisobutyric acid from isobutylene. Journal of Organic Chemistry (1958), 23 1488-9.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Benson JM, Barr EB, Krone JR: MTBE inhaled alone and in combination with gasoline vapor: uptake, distribution, metabolism, and excretion in rats. Res Rep Health Eff Inst. 2001 May;(102):73-94; discussion 95-109. Pubmed: 11504149 Link_out
    2. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979 Link_out
    3. NTP Toxicology and Carcinogenesis Studies of Isobutene (CAS No. 115-11-7) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1998 Dec;487:1-230. Pubmed: 12563344 Link_out
    4. Shigematsu Y, Sudo M, Momoi T, Inoue Y, Suzuki Y, Kameyama J: Changing plasma and urinary organic acid levels in a patient with isovaleric acidemia during an attack. Pediatr Res. 1982 Sep;16(9):771-5. Pubmed: 7133811 Link_out